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2 article(s) from Neudörfl, J-M

Control of asymmetric biaryl conformations with terpenol moieties: Syntheses, structures and energetics of new enantiopure C₂-symmetric diols

Y. Alpagut,
B. Goldfuss and
J.-M. Neudörfl

Beilstein J. Org. Chem. 2008, 4, No. 25, doi:10.3762/bjoc.4.25

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Graphical Abstract

Scheme 1: Atropisomeric BINOL and conformationally restricted, (−)-fenchone-based (M)-BIFOL.

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Scheme 2: Syntheses of (M)-BIMOL, (P)-BIVOL, (P)-BICOL, and (P)-BIMEOL.

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Figure 1: X-Ray crystal structure of (M)-BIMOL. An acetone molecule, binding to the external OH group, is omi...

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Figure 2: X-Ray crystal structure of (P)-BIVOL. A water molecule, binding to the external OH group, is omitte...

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Figure 3: X-Ray crystal structure of (P)-BICOL. A water molecule, binding to the external OH group, is omitte...

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Figure 4: X-Ray crystal structure of (P)-BIMEOL. An ethanol molecule, binding to the external OH group, is om...

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Figure 5: B3LYP/6-31++G**:AM1 optimized structure of (M)-BIMOL, E_rel. = 0.0 kcal/mol.

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Figure 6: B3LYP/6-31++G**:AM1 optimized structure of (P)-BIMOL, E_rel. = 1.3 kcal/mol.

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Figure 7: B3LYP/6-31++G**:AM1 optimized structure of (M)-BIVOL, E_rel. = 5.1 kcal/mol.

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Figure 8: B3LYP/6-31++G**:AM1 optimized structure of (P)-BIVOL, E_rel. = 0.0 kcal/mol.

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Figure 9: B3LYP/6-31++G**:AM1 optimized structure of (M)-BICOL, E_rel. = 5.8 kcal/mol.

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Figure 10: B3LYP/6-31++G**:AM1 optimized structure of (P)-BICOL, E_rel. = 0.0 kcal/mol.

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Figure 11: B3LYP/6-31++G**:AM1 optimized structure of (M)-BIMEOL, E_rel. = 5.4 kcal/mol.

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Figure 12: B3LYP/6-31++G**:AM1 optimized structure of (P)-BIMEOL, E_rel. = 0.0 kcal/mol.

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Scheme 3: Co-solvent adducts in the X-ray structures of (M)-BIMOL, (P)-BIVOL, (P)-BICOL, and (P)-BIMEOL.

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Full Research Paper

Published 10 Jul 2008

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An exceptional P-H phosphonite: Biphenyl- 2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper- catalyzed 1,4-additions

T. Kop-Weiershausen,
J. Lex,
J.-M. Neudörfl and
B. Goldfuss

Beilstein J. Org. Chem. 2005, 1, No. 6, doi:10.1186/1860-5397-1-6

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Graphical Abstract

Scheme 1: Monodentate phosphorus ligands, e.g. BINOL-based phosphoramidites or TADDOL-based phosphites, are h...

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Scheme 2: Modular phosphoramidites (R= NR'2) or phosphites (R= OR') from reactive chlorophosphite intermediat...

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Figure 1: X-ray crystal structure of BIFOP-Cl (1). Distances are given in Å. (BAA = biaryl angle between C₂-C₁...

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Figure 2: X-ray structures of BIFOP-Br (2). Distances are given in Å. (BAA = biaryl angle between C₂-C₁-C₁'-C₂...

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Scheme 3: Synthesis of biphenyl-2,2'-bisfenchol (BIFOL) based phosphane derivatives (BIFOPs).

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Figure 3: X-ray structures of BIFOP-H (3). Distances are given in Å. (BAA = biaryl angle between C₂-C₁-C₁'-C₂...

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Figure 4: X-ray structures of BIFOP-nBu (5). Distances are given in Å. (BAA = biaryl angle between C₂-C₁-C₁'-C...

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Figure 5: X-ray structures of BIFOP(O)-H (8). Distances are given in Å. (BAA = biaryl angle between C₂-C₁-C₁'...

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Figure 6: X-ray structures of phosphite BIFOP-OPh (6). Distances are given in Å. (BAA = biaryl angle between C...

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Figure 7: X-ray structures of phosphoramidite BIFOP-NEt2 (7). Distances are given in Å. (BAA = biaryl angle b...

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Figure 8: X-ray structures of BIFOP(O)-Cl (9). Distances are given in Å. (BAA = biaryl angle between C₂-C₁-C₁...

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Scheme 4: Geometries of BIFOP-systems with respect to biaryl dihedral angles (C₂-C₁-C_1’-C_2’, BAA), fenchyl-ar...

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Figure 9: Computed geometry (PM3) of plus-(P)-BIFOP-Cl with unnatural plus-(P)-biaryl conformation. Distances...

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Scheme 5: Biphenyl-2,2'-bisfenchol based phosphanes (BIFOPs) as chiral ligands in enantioselective Cu-catalyz...

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Scheme 6: Anharmonic B3LYP/6-31G^*(C,H,N,O,F,Cl,Br) /SDD(Cu) CO-stretching frequencies to assess metal to liga...

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Full Research Paper

Published 26 Aug 2005

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Control of asymmetric biaryl conformations with terpenol moieties: Syntheses, structures and energetics of new enantiopure C2-symmetric diols

An exceptional P-H phosphonite: Biphenyl- 2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper- catalyzed 1,4-additions

Control of asymmetric biaryl conformations with terpenol moieties: Syntheses, structures and energetics of new enantiopure C₂-symmetric diols